Glycoside of alpha-naphthylamine-4-sulfonic acid



Patented Sept. 21, 1954 2 689 847 UNITED STATES PATENT OFFICE GLYiJOSIDE OF a-NAPHTHYLAMINE-4- SULFONIO ACID Antonio Esteve, Barcelona, Spain, assignor to Laboratories m, Socit Anonyme, Geneva, Switzerland, a corporation of Switzerland No Drawing. Application February 18, 1952, Serial No. 272,276

Claims priority, application Switzerland April 20, 1951 1 Claim. (01. 260-211.5) l 2 The present invention relates to new derivatives 12.26 gr. of anhydrous a-naphthylamine--sulof a-naphthylamine-4-sulphonic acid, endowed phonate of sodium is made to react with 10 gr. with therapeutic properties, and to a process for Of anhydrous glucose, in 600 cm. of absolute alpreparing same. cohol in the presence of 1 gr. of ammonium chlo- The said new derivatives answer to the formula 5 ride. This is heated to boiling point with reflux NH-R in a steam bath, while stirring the reactive mixture continually during two hours. The mixture is then allowed to cool, a crystalline mass is formed which is isolated by filtration, it is Washed in alcohol and dried. A crystalline mass is obtained which is very soluble in water, little soluble SOPX in alcohol and in ether. This product decomposes in which R is a carbohydrate radical, for example Wlthout melting at 200 and its rotatory power that of a monosaccharide such as glucose, galac- 1S tose, xylose, that of a polysaccharide and X a hy- 18 drogen atom or an atom of a monovalent metal, D such as sodium, or an equivalent of a polyvalent metal, such as calciunii or an or an r a Its aqueous solutions are stable at ordinary ik i e e o nig ufid s ae efi ve in the treatment 20 gfi g even at low as that of gastnc and prevention of haemorrhages, they increase Its constituting fo ula is as follows: the speed of coagulation of the blood and reduce the bleeding time; furthermore, they are devoid of HN-OH-(OHOH)sCH-CH2OH toxicity.

The process of preparation of these new derivatives of a-naphthylamine-e-sulphonic acid consists in condensating a carbohydrate with a-naphthyl'amme-d-sulphonic acid or one of its salts or one of its esters or one of its amides. some The said condensation may be carried out within a solvent, which may be water or prefer- Whatlclalm 1S: ably an anhydrous solvent; it may also be carried The glufwslde of anaphthylamme4sulpho out in the absence of any solvent or other body. mate of 5001mm- It may be carried out with the assistance of heat, in the presence of a dehydrating agent, such as References Cited in the file of this patent ammonium chloride, potassium bisulphate, zinc chloride or another salt of similar properties. UNITED STATES PATENTS How the process according to the invention Number Name Date may be carried out will now be explained, by Way 2,141,843 Meyer et a1 Dec. 27, 1938 of example, in connection with the preparation of 2,167,? 19 Klingel et al Aug. 1, 1939 the glucoside of anaphthylamine-4-sulphonate 2,193,433 Salzberg Mar. 12, 1940 of sodium. 2,268,780 Shonle Jan. 6, 1942 

